It's been bugging me for a while, but Google has been no help. It was a fake documentary that came out in the late '90s/early '00s about an aspiring actress in New York City and her gay best friend. The documentary filmmaker in the movie first noticed her in a cereal commercial and decided to make a documentary about her. Much of the movie basically just detailed how much it sucks being an aspiring actor in New York City (or anywhere), but some of the most identifiable parts were: The gay best friend got work as an extra on a soap opera but overacted so badly in the background (distracting from the main actors on screen), he was immediately fired. The gay best friend had a relationship with a more successful and deeply closeted actor who dumped him so his career wouldn't be harmed. The gay best friend proceeded to write and star in a popular one-man show about his heartbreak. Hollywood optioned the show, but turned it into a straight romance starring John Cusack and Mira Sorvino, both of whom appeared in cameos in this movie. I checked the IMDB pages for both of them, and this movie didn't appear, so I assume they were uncredited. Anyone have any ideas?
FAMOUS (2000)? It stars Laura Kirk. A documentarian decides to follow the career of New York actress Lisa Picard, believing she is on the brink of fame. Instead, he bears witness to Lisa's continued, humorous, struggles as an actress, as well as the conflict that arises when Lisa's best friend Tate hits it big with an off-Broadway one-man show. John Cusack is not listed in the cast but Mira Sorvino is. See here: